EP0084224A1 - Sulfonamid-Herbizide - Google Patents

Sulfonamid-Herbizide Download PDF

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Publication number
EP0084224A1
EP0084224A1 EP82306492A EP82306492A EP0084224A1 EP 0084224 A1 EP0084224 A1 EP 0084224A1 EP 82306492 A EP82306492 A EP 82306492A EP 82306492 A EP82306492 A EP 82306492A EP 0084224 A1 EP0084224 A1 EP 0084224A1
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EP
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Prior art keywords
compound
och
alkyl
formula
aminocarbonyl
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Granted
Application number
EP82306492A
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English (en)
French (fr)
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EP0084224B1 (de
Inventor
Rafael Shapiro
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to AT82306492T priority Critical patent/ATE22684T1/de
Publication of EP0084224A1 publication Critical patent/EP0084224A1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings

Definitions

  • This invention relates to herbicidal sulfonamides, and, more particularly, to substituted triazinyl or pyrimidinyl sulfonylurea ccmpounds which are selective pre-emergence and/or post-emergence herbicides.
  • U.S. Patents 4,127,405 and 4,169,719 disclose herbicidal methoxymethylpyrimidine sulfonylurea compounds of the type which contain a -CH 2 0CH 3 heterocyclic substituent.
  • This invention relates to novel compounds of Formula I, suitable agricultural compositions containing them, and their method of use as general and/or selective pre-emergence and/or post-emergence herbicides or plant growth regulants.
  • the compounds of Formula I may be prepared by the reaction of an appropriately substituted sulfonyl isocyanate of Formula II with an aoprocriate 2-amias- heterocycle of Formula III according to Eouation 1:
  • Equation 1 The reaction of Equation 1 is best carried-cut in an inert aprotic solvent such as methylene chloride, tetrahydrofuran, acetonitrile at a temperature between O 0 and reflux, preferably between 20 and 80 Q .
  • a catalytic amount of DABCO (1,4-diazabicyclo[2.2.2]octane) may be used to accelerate the reaction.
  • the products are insoluble in the reaction solvent, they may be isolated by simple filtration. When the products are soluble in the reaction solvent they are isolated by evaporation of the solvent and trituration of the residue with solvents such as 1-chlorobutane, ethyl ether or methanol and filtration.
  • isocyanates and isothiocyanates (II) are described in the following: U.S. 4,127,405, U.S. 4,169,719, EP-A-7,687, EP-A-13,480, EP-A-23,141, EP-A-23,422, EP-A-30,141, and GB-A-2,065,116 to which the reader is referred for further information.
  • the sulfonyl isocyanates of Formula IIa which are disclosed in our EP-A-44,212, may be prepared analogously to the teachings of U.S. 4,127,405. wnerein
  • Triazines of Formula IIIb may be prepared according to the methods outlined in Equations 2 and 3.
  • Equation 2a The reaction of Equation 2a is carried out according to the teachings of J. M. McElvain and R. L. Clarke, J. Amer. Chem. Soc., 69, 2657 (1947), in which the preparation of ethyl diethoxyiminoacetate is described.
  • the intermediate N-cyanoimioates of Formula VI may be prepared according to the teaching of D. Lwowski in Svnthesis, 1971, 263, by reacting V with cyanamide at pH 5.5, and these may be condensed according to reaction 2c with the appropriate compound of Formula VII in an alcoholic solvent at 25 to 80°C to provide the appropriate triazines.
  • Equation 3a described for substituted acetonitriles by F. C.
  • the free base may be carried on through reactions 2b and 2c, or, alternatively, converted to the amidinium hydrochloride salts (VIII) as described in the aforementioned reference.
  • the compounds of Formula VIII may be converted to the compounds IIIb by the reaction of Equation 3c, in which VIII is contacted with a compound of Formula IX at 0 to 30°C in the presence of 3-4 equivalents of the appropriate sodium alkoxide in the appropriate alcohol.
  • the product may be isolated by evaporation of solvent, neutralization with aqueous acetic acid, and filtration.
  • the compounds of Formula IIIc may be prepared by the sequence of reactions outlined in Equation 4.
  • Equations 4a and 4b are carried out as described by W. Braker, et al., loc. cit.
  • the compounds of Formula IIId may be prepared by similar meracrs snewn in Equation 5.
  • Equations 5a and 5o are conducted as described for 2-amino-4-hydroxy-6-dimethoxy- methylp-yrimidine (J. I. De Graw ano V. H. Brown, J. Het. Chem., 13, 439 (1976)).
  • the silver salt of XIII may be prepared by addition of ammonia to an aqueous solution of XIII and an equivalent amount of silver nitrate.
  • the dried silver salt may be contacted witn one equivalent of methyl or ethyl iodide in a nonpolar solvent such as benzene at 25 to 80°C to provide pyrimidines of Formula IIId after purification by column chromatography or recrystallization.
  • the compounds of Formula IIIc may be prepared via the corresponding chloropyrimidines (IIIe). These may be obtained by the reaction of Equation 6a, in which a compound of Formula XIII is contacted with 2-5 equivalents of phosphorous oxychloride at 20-40°C for 3-30 hours. The product is isolated by removal of excess POC1 3 in vacuo, treatment of the residue with ice-water, extraction into an organic solvent, concentration, crystallization or column chromatography. The chloropyrimioines may then be converted to the compounds of Formula IIId by contacting with one equivalent of the appropriate sodium alkoxide in alcohol at 0-30°C followed by concentration and precipitation with ice-water.
  • Cyclic acetals of Formula IIIe may be prepared from compounas of Formula IIIa according to Equation 7 by acetal exchange.
  • the reaction of Eauation 7 is carrieo out c/ heading the acyclic acetal in an inert solvent in the oresence of one equivalent of a compous of Formula XV and sligntly more than one equivalent of an acioic catalyst, such as p-toluenesulfonis adis or boron trifluoride etherate with distillation of the by-product alcohol.
  • the compound of Formula IIIe may oe isolated by extraction with an organic solvent, and purified by crystallization or column chromatography.
  • N-methyl compounds of Formula IIIg may be accomplished by the procedure shown in Equation 8.
  • the reaction of Equation Sa may be carried out by stirring a mixture of IIIf with one equivalent each of sodium hydride and dimethyl carbonate for 1-3 days in an inert solvent such as tetrahydrofuran or dime- thylfcrmamide.
  • the product of Formula XVI may be isolated by evaporation of solvent, neutralization with aqueous acetic acid, and filtration of the product.
  • the reaction of Equation 8b is performed by adding XVI to a slurry of one equivalent of sodium hydride in tetrahydrofuran at 0-30°, stirring for 1/2 hour, anJ adding methyl iodide, heating to reflux for 1-20 hours, and stirring with water and aqueous sodium hydroxide for 1-20 hours at 20-30°.
  • the product is isolated by evaporating the solvent, adding ice-water, and filtering.
  • the compounds of Formulae IIIh and IIIi may be prepared by the reactions of Equation 9, which are carried out by analogy with the procedures.described for the reactions of Equations 5c and 5d.
  • Compounds of Formula Ib may be prepared by acidic hydrolysis of compounds of Formula Ia according to Equation 10:
  • the reaction of Equation 10 is preferably carried out by stirring a solution or suspension of Ia in a polar protic solvent, e.g. aqueous acetone, containing a catalytic amount of a strong mineral acid, such as hydrochloric or sulfuric acid, at 0 to 30°C, followed by concentration and filtration of the product.
  • a polar protic solvent e.g. aqueous acetone
  • a catalytic amount of a strong mineral acid such as hydrochloric or sulfuric acid
  • the compounds of Formula Ib may be in turn converted to compounds of Formulae Ic, Id, or Ie according to Equation 11;
  • Equation 12a The reaction of Equation 12a is conducted in the same manner as described for Equation 1.
  • the resulting compounds of Formula XIX may be converred to compounds of Formula If by contacting them with 3-5 equivalents of diisobutyl aluminum hydrioe in an ethereal solvent at -20 to 20°, after which-the reaction mixture is quenched with aqueous mineral acid and extracted with an organic solvent.
  • the product may be isolated by evaporation of solvent and crystallization.
  • Eauation 13 outlines the preparation of the compounds of Formula XVIII.
  • the pyrimidine of Formula XX is describee by Z. Bucesinsky and F. Roubinek, in Coll. Czech. Chem. Comm., 26, 2871 (1961). This may be heated in an autoclave at 80 to 140° with ammonia or methyl amine to afford the amino acids of Formula XXI. These may be esterified in the usual manner with methanol and acid, followed by evaporation of solvent, neutralization and filtration to afford the compounds of Formula XVIIIa.
  • the reaction of Equation 12b is conducted according to the procedure described for Equation 6b.
  • the aqueous phase was washed with ether and acidified with 20 ml of acetic acid, extracted with 600 ml of methylene chloride, the organic layer was dried (MgSO 4 ) and concentrated, and the residue was heated at 80-90° with 28 g of guanidine carbonate for 1 hour. Addition of ice-water to the cooled reaction mixture prectiptated the product, which was filterec and dried to afford the title compound, m.p. 109-110. 5°.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and tne like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, can contain from about 0.1% to..99N by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide,” 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration”, Chemical Engineering, December 4, 1967, pp. 147ff. and “Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.
  • the ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
  • the ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter.
  • the product is reblended before packaging.
  • a slurry of wettable powder containing ⁇ 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • the ingredients are blended, hammer-milled and then moistened with about 12% water.
  • the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets aoout 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings).
  • the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recyclec.
  • the ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns.
  • the resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
  • the ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • the active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
  • the ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
  • the salt is added directly to the water witn stirring tc produce the solution, which may then be packaged for use.
  • the active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
  • the ingredients are blended and milled to pass through a 100 mesh screen.
  • This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material.
  • the fluidization and spraying are continued until granules of the desired size range are made.
  • the spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced tc the desired level, generally less than 1%.
  • the material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
  • the ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening).
  • the concentrate may be formulated further if necessary.
  • the ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns.
  • the material is sifted through a U.S.S. No. 50 screen and then packaged.
  • the ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size.
  • the material is reblended and then packaged.
  • the ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns.
  • the product can be used directly, extended with oils, or emulsified in water.
  • the compounds of the present invention are highly active herbicides. They have utility for broad- spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive- in theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds are useful for selective pre- or post-emergence weed control in crops, such as cotton, soybeans and wheat.
  • the rates of application for the compounds of the invention are influenced by a number of factors, including their use whether as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulation ingredients, mode of application, amount of foliage present, etc.
  • the subject compounds should be applied at levels of around 0.01 to 5 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required.
  • the compounds of the invention may be used in combination with any other commercial herbicide, such as, for example those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
  • any other commercial herbicide such as, for example those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
  • cotton having five leaves including cotyledonary ones
  • bush beans with the third trifoliolate leaf expanding crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morning g lory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed.
  • the accompanying descriptive symbols have the following meanings:
  • Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil.
  • One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds.
  • the other pan was planted with cotton, soybeans, purple nutsedge (Cvoerus rotundus), and several broadleaf weeds.
  • the following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusaalli), wild oats (Avena fatua), johnsongrass (Sorghum hale- implica), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium).
  • a 12.5 cm diameter plastic pot was-also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four
  • Two ten-inch in diameter plastic pane lined with polyethylene liners were filled with prepared Fallsington silt loam soil.
  • One pan was planted with seeds of wheat (Triticum aestivum), barley ( vulaare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alooecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Aaroovron reoens), Italian ryegrass (Lolium multi- florum) and ripgut brome (Bromus ricidus).
  • the other pan was planted with seeds of Russian thistle (Salsola kali), tansy mustard (Descuraina pinnata), Galium apa- rine, tumble mustard (Sisymbrium altissium) kochia (Kochia scoparia), shepherd's purse (Capsella bursa- pastoris), Matricaria inodora, black nightshade (Solanum niarum), yellow rocket (Barbarea vulaaris), wild mustard (Brassica kaber) and wild buckwheat (Polvaonum convolvulus).
  • Russian thistle Salsola kali
  • tansy mustard Descuraina pinnata
  • Galium apa- rine tumble mustard
  • kochia Kechia scoparia
  • shepherd's purse Capsella bursa- pastoris
  • Matricaria inodora black nightshade (Solanum niarum)
  • yellow rocket Barbarea vulaaris
  • wild mustard Brassica kaber
  • test compounds were diluted with a non-phytotoxic solvent and sprayed over-the-top of the pans.
  • An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. The recorded data are presented in Table C. Several of the compounds tested exhibit utility for post-emergence weed control in wheat.
  • test chemicals dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species.
  • plants were observed for rapid burn injury.
  • Approximately fourteen days after treatment all species were visually compared to untreated controls and rated for response to treatment.
  • the rating system was as described previously for Test A. The data are presented in Table D.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fertilizers (AREA)
EP82306492A 1981-12-07 1982-12-06 Sulfonamid-Herbizide Expired EP0084224B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82306492T ATE22684T1 (de) 1981-12-07 1982-12-06 Sulfonamid-herbizide.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US32801881A 1981-12-07 1981-12-07
US43403882A 1982-10-20 1982-10-20
US434038 1982-10-20
US328018 1989-03-23

Publications (2)

Publication Number Publication Date
EP0084224A1 true EP0084224A1 (de) 1983-07-27
EP0084224B1 EP0084224B1 (de) 1986-10-08

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EP (1) EP0084224B1 (de)
JP (1) JPS58116472A (de)
AT (1) ATE22684T1 (de)
AU (1) AU553872B2 (de)
BR (1) BR8207018A (de)
CA (1) CA1221698A (de)
DE (1) DE3273625D1 (de)
DK (1) DK536582A (de)
ES (1) ES517931A0 (de)
GB (1) GB2110692B (de)
GR (1) GR77852B (de)
IL (1) IL67423A (de)
NZ (1) NZ202716A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106512A2 (de) * 1982-09-10 1984-04-25 E.I. Du Pont De Nemours And Company Herbizide ortho-alkyl- und ortho-alkenyl-substituierte Benzolsulfonamide
EP0164269A2 (de) * 1984-06-07 1985-12-11 E.I. Du Pont De Nemours And Company Herbizide Sulfonamide
EP0176304A1 (de) 1984-09-17 1986-04-02 E.I. Du Pont De Nemours And Company Herbizid wirkende Pyrazolsulfonamide
EP0177163A2 (de) 1984-08-27 1986-04-09 E.I. Du Pont De Nemours And Company Herbizide Acetale und Ketale
EP0205323A2 (de) * 1985-06-07 1986-12-17 E.I. Du Pont De Nemours And Company Cyanoheterocyclische Sulfonylharnstoffe
EP0209230A1 (de) 1985-05-30 1987-01-21 E.I. Du Pont De Nemours And Company Herbizid wirksame Sulfonamide
EP0271208A1 (de) 1986-11-12 1988-06-15 E.I. Du Pont De Nemours And Company Herbizide Pyridin-N-oxid-sulfonylharnstoffe
EP0155767B1 (de) * 1984-02-21 1990-08-16 E.I. Du Pont De Nemours And Company Herbizide Sulfonamide
EP0146263B1 (de) * 1983-11-15 1991-05-15 E.I. Du Pont De Nemours And Company Herbizide substituierte Thiophen, Furan- und Pyrrol-Sulfonamide
US20190011067A1 (en) * 2016-01-19 2019-01-10 Flecotec Ag Method for connecting two flexible tubular containers

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4618363A (en) * 1982-01-25 1986-10-21 Ciba-Geigy Corporation N-phenylsulfonyl-N'-triazinylureas
EP0098569A3 (de) * 1982-07-08 1984-12-19 Hoechst Aktiengesellschaft Neue heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft
ZA836639B (en) * 1982-09-08 1984-05-30 Ciba Geigy Ag Novel sulfonylureas
US4579583A (en) * 1982-09-08 1986-04-01 Ciba-Geigy Corporation Novel sulfonylureas
US4515626A (en) * 1982-10-06 1985-05-07 Ciba Geigy Corporation N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity
US4639264A (en) * 1983-08-26 1987-01-27 Ciga-Geigy Corporation Herbicidal N-arylsulfonyl-N'-(4-mercaptomethylpyrimdinyl)-ureas
JPS60197676A (ja) * 1984-03-16 1985-10-07 Ishihara Sangyo Kaisha Ltd 置換チオフエンスルホンアミド系化合物及びそれらを含有する除草剤
JPS60193983A (ja) * 1984-03-15 1985-10-02 Ishihara Sangyo Kaisha Ltd 置換チオフエンスルホンアミド系化合物及びそれらを含有する除草剤
JPS60139691A (ja) * 1983-12-27 1985-07-24 Ishihara Sangyo Kaisha Ltd 置換チオフエンスルホンアミド系化合物及びそれらを含有する除草剤
JPS60166668A (ja) * 1984-02-10 1985-08-29 Nippon Tokushu Noyaku Seizo Kk ２−アルコキシアミノスルホニルベンゼン−スルホニルウレア誘導体、その製法及び除草剤
EP0158600B1 (de) * 1984-04-11 1991-04-03 Ciba-Geigy Ag Verfahren zur selektiven Unkrautbekämpfung in Nutzpflanzenkulturen
DE3528100A1 (de) * 1985-08-06 1987-02-19 Bayer Ag 1-(2-oxyaminosulfonylphenylsulfonyl) -3-triazinyl-harnstoffe
US4566898A (en) * 1984-09-07 1986-01-28 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
AU4789685A (en) * 1984-09-28 1986-04-10 E.I. Du Pont De Nemours And Company Heterocyclic sulphonamide derivatives
US4744814A (en) * 1984-12-06 1988-05-17 Ishihara Sangyo Kaisha N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-trifluoromethylpyridine-2-sulfonamide or salts thereof, herbicidal composition containing the same
CA1232273A (en) * 1984-12-11 1988-02-02 James V. Hay Herbicidal sulfonamides
US4743290A (en) * 1986-04-21 1988-05-10 E. I. Du Pont De Nemours And Company Thiophenesulfonamide herbicides
US4877440A (en) * 1985-05-29 1989-10-31 E. I. Du Pont De Nemours And Company Thiophenesulfonamide herbicides
US4900353A (en) * 1986-11-12 1990-02-13 E. I. Du Pont De Nemours And Company Herbicidal pyridine N-oxide sulfonylureas
US5209770A (en) * 1989-05-26 1993-05-11 E. I. Du Pont De Nemours And Company Herbicidal pyridinesulfonylureas
US5102444A (en) * 1986-12-08 1992-04-07 E. I. Du Pont De Nemours And Company Herbicidal pyridinesulfonylureas
US4948419A (en) * 1986-12-18 1990-08-14 E. I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamides
US4838926A (en) * 1986-12-18 1989-06-13 E. I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamides
FR2617167B1 (fr) * 1987-06-25 1989-11-24 Rhone Poulenc Agrochimie Herbicides de type sulfonyluree, leur preparation, les compositions les contenant et leur utilisation
ES2061570T3 (es) * 1987-08-05 1994-12-16 Hoechst Schering Agrevo Gmbh Sulfonamidatos de fenilo con sustituyentes heterociclicos, procedimiento para su preparacion y su utilizacion como herbicidas y reguladores del crecimiento de las plantas.
EP0308371A1 (de) * 1987-09-18 1989-03-22 Ciba-Geigy Ag 4-Azasaccharine, 4-Aza-dihydro-oder-tetrahydrosaccharine und Verfahren zu deren Herstellung
ATE111463T1 (de) * 1989-06-06 1994-09-15 Ciba Geigy Ag Sulfonylharnstoffe.
US5529976A (en) * 1990-01-10 1996-06-25 Hoechst Aktiengesellschaft Pyridyl sulphonyl ureas as herbicides and plant growth regulators
EP0510032B1 (de) * 1990-01-10 1996-11-13 Hoechst Schering AgrEvo GmbH Pyridylsulfonylharnstoffe als herbizide und pflanzenwachstumsregulatoren, verfahren zu ihrer herstellung und ihre verwendung
EP0555770A1 (de) 1992-02-14 1993-08-18 Hoechst Schering AgrEvo GmbH N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
US5847146A (en) * 1992-02-14 1998-12-08 Hoechst Schering Agrevo Gmbh N-heteroartyl-n'-(pyrid-2yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators
WO1995006049A1 (de) * 1993-08-24 1995-03-02 Hoechst Schering Agrevo Gmbh N-heteroaryl-n-(pyrid-2-yl-sulfonyl)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren

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EP0009419A1 (de) * 1978-09-27 1980-04-02 E.I. Du Pont De Nemours And Company Sulfonamide für die Landwirtschaft, deren Herstellung und Verwendung
EP0023140A2 (de) * 1979-07-20 1981-01-28 E.I. Du Pont De Nemours And Company Herbizide Sulfonamide, deren Herstellung und Verwendung, und sie enthaltende Zusammensetzungen
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Cited By (13)

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Publication number Priority date Publication date Assignee Title
EP0106512B1 (de) * 1982-09-10 1988-05-18 E.I. Du Pont De Nemours And Company Herbizide ortho-alkyl- und ortho-alkenyl-substituierte Benzolsulfonamide
EP0106512A2 (de) * 1982-09-10 1984-04-25 E.I. Du Pont De Nemours And Company Herbizide ortho-alkyl- und ortho-alkenyl-substituierte Benzolsulfonamide
EP0146263B1 (de) * 1983-11-15 1991-05-15 E.I. Du Pont De Nemours And Company Herbizide substituierte Thiophen, Furan- und Pyrrol-Sulfonamide
EP0155767B1 (de) * 1984-02-21 1990-08-16 E.I. Du Pont De Nemours And Company Herbizide Sulfonamide
EP0164269A2 (de) * 1984-06-07 1985-12-11 E.I. Du Pont De Nemours And Company Herbizide Sulfonamide
EP0164269A3 (en) * 1984-06-07 1986-04-23 E.I. Du Pont De Nemours And Company Herbicidal sulfonamides
EP0177163A2 (de) 1984-08-27 1986-04-09 E.I. Du Pont De Nemours And Company Herbizide Acetale und Ketale
EP0176304A1 (de) 1984-09-17 1986-04-02 E.I. Du Pont De Nemours And Company Herbizid wirkende Pyrazolsulfonamide
EP0209230A1 (de) 1985-05-30 1987-01-21 E.I. Du Pont De Nemours And Company Herbizid wirksame Sulfonamide
EP0205323A3 (de) * 1985-06-07 1988-05-11 E.I. Du Pont De Nemours And Company Cyanoheterocyclische Sulfonylharnstoffe
EP0205323A2 (de) * 1985-06-07 1986-12-17 E.I. Du Pont De Nemours And Company Cyanoheterocyclische Sulfonylharnstoffe
EP0271208A1 (de) 1986-11-12 1988-06-15 E.I. Du Pont De Nemours And Company Herbizide Pyridin-N-oxid-sulfonylharnstoffe
US20190011067A1 (en) * 2016-01-19 2019-01-10 Flecotec Ag Method for connecting two flexible tubular containers

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AU9115182A (en) 1983-06-16
IL67423A (en) 1986-09-30
CA1221698A (en) 1987-05-12
NZ202716A (en) 1985-11-08
ES8401477A1 (es) 1983-12-16
JPS58116472A (ja) 1983-07-11
BR8207018A (pt) 1983-10-11
DE3273625D1 (en) 1986-11-13
AU553872B2 (en) 1986-07-31
EP0084224B1 (de) 1986-10-08
DK536582A (da) 1983-06-08
GR77852B (de) 1984-09-25
GB2110692A (en) 1983-06-22
IL67423A0 (en) 1983-05-15
GB2110692B (en) 1985-07-17
ES517931A0 (es) 1983-12-16
ATE22684T1 (de) 1986-10-15

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